


How to Train Your Guardian

by DemonicClaymore, SuperPuppies



Category: How to Train Your Dragon (2010), Rise of the Guardians (2012)
Genre: Alternate Universe, Discovery, Dragons, Frostcup - Freeform, FrostedCup, FrostedToothCup, JacCup, Jack/Hiccup - Freeform, M/M, Male Friendship, Male Homosexuality, Other, Roleplay, ToothUp, Toothcup, Yaoi, dragon rider, how to train your gaurdian
Language: English
Status: In-Progress
Published: 2013-05-07
Updated: 2013-06-26
Packaged: 2017-12-10 16:20:15
Rating: Explicit
Warnings: Underage
Chapters: 5
Words: 20,159
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/788033
Author URL: https://archiveofourown.org/users/DemonicClaymore/pseuds/DemonicClaymore, https://archiveofourown.org/users/SuperPuppies/pseuds/SuperPuppies
Summary: <blockquote class="userstuff">
              <p>Hiccup and Toothless fly into an aurora portal that drops them in Jack Frost's world. The three become friends and realize they all have a lot to teach each other about all sorts of things.</p>
            </blockquote>





	1. Introductions can sometimes hurt.

**Author's Note:**

> Unrated so far because we haven't gotten very far in it, though we think it will end up being an adult slash fic between jack and hiccup at least. This is an RP between me and my friend, SuperPuppies. We hope you enjoy!
> 
>  **Characters & Writers**  
> DemonicClaymore = Jack and Toothless  
> SuperPuppies = Hiccup

**Summary for the Chapter:**

> Hiccup and Toothless fly off from Berk after Hiccup gets an uncomfortable lecture. They sore through the sky while Hiccup rants until they see a strange section of rainbow lights in the sky and what appears to be the form of a boy in the midst of them. 
> 
> Jack Frost was minding his own business when suddenly he's knocked from the sky by some terrible force and his staff is knocked from his grasp. Free falling is more fun when you know you have a parachute.

If anyone else in Berk was son of the great chief, Stoick the Vast, they would likely be thrilled to hear that their father was ready to have a heart to heart talk about becoming a man. However, given the uncomfortable nature of the relationship between the enormous man and his tiny son, it was no real surprise when the boy only listened nervously until the mention of women came into play. At that point, Hiccup had rushed out the door with an unreasonable excuse, mounted his dragon and took off in record time.

Hiccup urged toothless higher into the sky. Anything to put as much distance between himself and his father. "Oh god, ugh…." Hiccup ran a hand over his face. "What was that about? Why now? Why!"

Toothless flew up into the clouds and kept going until there was a sea of fluffiness between them and the world below. Then, he glanced back over his shoulder at his disgruntled rider. He growled and tilted his head to the side. His eyes were large and curious. ‘What’s wrong?’ is what he tried to ask. But alas, his human companion was a little to dense to understand a complex language like Dragon. For now, he knew that tilting is head this way or that, opening his mouth wider or dilating his eyes a certain way seemed to get is points across to the boy.

Hiccup leaned down resting his forehead atop Toothless'. "Sorry buddy, he just gave me a bit of a scare back there." Hiccup heaved a heavy sigh. "I mean, not to boast or anything, but I am clearly the smartest person in the village. Okay, so Fishlegs may have the whole book of dragons memorized and I don't. -But I generally know everything else. So what on Odin's green earth makes dad think I need to have 'the talk' at all and right now of all times!" Hiccup sat back up and let the wind wash over his face.

Toothless licked his lips to wet them. He had no idea what Hiccup was going on about. What was ‘The Talk’ and why was his rider so afraid of it? He thought humans loved to talk. Wasn’t Hiccup always complaining that his father didn’t want to talk to him? 

The dragon shook his head and made a small growl. He looked back ahead. Regardless of his understanding, he was sure Hiccup had much more to say on the matter and it would be fun to listen to.

Hiccup decided to focus on other things. Yep, that’s what he need to do. Don’t think about it then it's not a problem. That was the viking way, right? Sure it was! So, yes. Other things. Other things.  
Hiccup scratched his chin while trying to think of something, anything else. But no! All that just kept booming in his head was his father's voice. ' So you see son after a Viking has asserted himself to his woman of choice. He must claim her and to do so...' 

"AAAAAAHHH, NO. Stop it! I don't need THIS!!!!"

The sudden sound of Hiccup’s shrieking left the Nightfury feeling a little unstable and on edge. His wings had clapped in for just a second, which made for some turbulence. He quickly caught himself though and growled back over his shoulder at the Viking on his back. ‘Odin’s beard boy! Are you trying to give me a heart attack!?’ 

The turbulence caused Hiccup to tighten his grip on the riding harness. Toothless growled up at him and Hiccup smiles softly. "Sorry buddy." He petted Toothless' head in apology. 

Still though, his fathers voice would not leave him. Hiccup screamed in frustration again rubbing his hand fiercely over his face. What was wrong with his father? Was he trying to give him nightmares?

Toothless let out a dragony sigh and turned to face forward again. It was no use trying to control a human. They always just sort of did what they wanted, even when it didn’t seem to make much sense. Then, from deep inside his belly Toothless began to purr. The vibration lifted up and out of his chest through his mouth. There, in front of the two flyers, was the strangest and most beautiful thing the young dragon had ever seen. 

A rainbow of colors all dancing together in swirls of misty ribbon captivated Toothless. He began flying straight toward the lights.

As Toothless purred a scenes of calm washed over hiccup. The light playing in the sky before them held his attention. Suddenly he had the urge to fly through them, become a part of them. 

Toothless rushed forward and nuzzled the rainbow clouds with his nose. He glided effortlessly through their ribbons and sang softly within the aurora’s body.

As they began to play amongst the light, Hiccup laughed whole heatedly. He hadn't felt this free in a very long time. Then there directly ahead of them the lights began to swirl and bend, making what looked like a boy.

Toothless’ eyes grew wide as he focused on the same form that his rider was gawking at. ‘What is that?’ His head tilted slightly to the side. As he looked closer he could see that it looked like a human. ‘Up here!? In the clouds?’ The idea was preposterous. All dragons knew that humans couldn’t fly. Yet, there it was: the impossible! Right before his very eyes.  
The dragon growled his concerns to Hiccup. Should he fly closer? Stop and say hello? Avoid him? He wasn’t rightfully sure.

Hiccup urged Toothless closer. "Co me on, Buddy. Let’s check it out." His curiosity was getting the best of him.

It wasn’t a moral struggle for the Nightfury. Toothless pushed forward and flew ever closer to the boy in the rainbow. His senses were usually pretty spot-on when it came to warnings of danger and he felt completely relaxed. He didn’t see a reason not to fly right up to the strange flying boy and say hello. As he moved closer, the tip of his nose started to chill. Then, all around the two, the air started to get colder and colder. Toothless shivered and watched carefully, as the boy in the sky seemed to get clearer but not closer. Was he flying away from them?

Hiccup shivered in the sudden cold, but was more confused how the boy seemed to be staying so far ahead of them. Shifting his foot to force Toothless' tail into a sharper position, he pushed them forward at a much faster speed. Hiccup was going to catch this flying boy!

The boy came in to clear view after just a second. His form was indeed floating in the sky. He was wearing some strange kind of blue coat and had hair white as snow. He was carrying some sort of stick and looking down at something below. Suddenly, Toothless had a fun idea. ‘I should knock him out of the sky!’ The dragon grinned and growled as he made his way through a seemingly endless tunnel of color. Then, without warning, it was nighttime all around them and the floating boy was getting closer at record speed.

Hiccup pulled back on Toothless. Suddenly very unnerved by the other boy who was coming straight at them. Their surroundings seemed to be shifting and he was having a very hard time recognizing anything around him.

 

Jack Frost had been watching Sadman’s handy work for the last hour or so and had finally stopped chasing his golden strings and creations. Now, he was looking over the sleepy town where Jamie lived and his pond was near. If it could be said the mischievous spirit had a home, it was here. 

The frosty child was taking note of a pattern he thought might be fun to fly that night when he frosted everything over before morning burnt away his masterpiece when a strange noise caught his attention. He looked up and over just in time to see something huge barreling towards him. “What the-?” 

Before winter’s helper had a chance to even consider fleeing, he was struck by the unidentified flying object at full force and all three of the life forms came toppling to the ground.  
Jack’s senses came back as he freefell. He looked over and saw his staff. His staff was several yards away. “No!” he yelled and reached out for his staff to no avail. Still, he kept trying. 

Hiccup tightened his grip on Toothless as they slammed into the boy. Toothless's wings froze and became heavy. They began dropping like stones. Hiccup tried to help Toothless shake the frost off his wings as they tumbled through the air.

The boy yelled and Hiccup looked over as the panic stricken boy reached out for the stick he had been holding.

Jack reached out with all his might but he wasn’t even close to grabbing his staff. 

Meanwhile, Toothless was having no trouble now that the ice was gone. His wings reached out, steadied themselves, and he leveled out. All the while the strange boy kept falling.

Hiccup let himself breath now that they weren't tumbling to their deaths any more. Though the same couldn't be said for the boy, so with a sigh, Hiccup leaned into Toothless. "Let’s go get him buddy."

Toothless tightened his wings and they shot down through the air. The boy had already fallen quite a bit further than they had and it was a task to catch up. Before the boy hit the top of the trees though, Toothless had managed to catch the stranger and flew up to level himself again.

“Aghhh---!---oh….” Jack looked up and saw that a giant lizard thing was now carrying him. He might have pondered it longer but his head snapped to the side. “No. Where-?” He began looking. ‘Where did it fall!?’ Panic rose up in his chest.

Toothless looked down to make sure he caught his target, then up to Hiccup with a smile. ‘Got him,’ he growled.

Hiccup smiled at Toothless' grin. They had they boy, so at least they didn't have to feel responsible for him if he had well died. "Let's find a place to set down and meet our new friend,” he said with a smile. Then leaning over to one side he looked down at the boy and called. "We'll have you down in just a second so hang on."

Toothless turned and stared heading for a patch of ground up on a hill that looked safe and easy to get to. He dropped the boy off first, then circled around and landed next to him.

The dragon was impressed with himself but Jack was on edge. He looked towards the woods and grabbed his head. His icy white locks messed between his knuckles. “No. No. No. No.”

The sight made Toothless cock his head as he allowed his rider off.

Hiccup jumped to the ground with a smile as he headed for the apparently upset boy. "What’s wrong? Are you hurt?" Hiccup asked coming to a stop in front to the white haired boy who really wasn't all that different looking from Hiccup. Bare foot, white hair and maybe a little thinner but that was about it.

“I lost it. I can’t loose it.” Jack took a step forward and fell on his face. When he looked up, he had a face of honest shock. He hadn’t ever been up and about without his staff before. Moving didn’t feel the same. Walking sure didn’t at the vary least. His ability to tap into the winds was gone. So, like a dog that just lost its tail, Jack stood and tried again. “Oomph!”

Hiccup stared wide-eyed for a moment before reaching down to help the boy up. "What did you lose? That stick you where holding? Is it important? " Hiccup brushed some grass and dirt off the other boys shirt.

Toothless thought about the stick he’d seen falling and noticed the boy’s staff was gone. ‘Is he making all that fuss over a stick?’ he wondered.

Jack looked at the boy who was full on touching him and tilted his head to the side. “You… see me? Who are-?” Then his attention reverted. “My staff!” He grabbed Hiccup by the shoulders. “Did you see where it fell?!”

Hiccup looked at the boy now very confused. Did he just ask if I could see him? He glanced back at Toothless then back to the boy. "Of course I can see you, I can see Changewings pretty well too but I'm afraid I didn't see where your stick fell."

Jack growled and tossed his hands to his sides. “Darn it!” 

This display made Toothless growl. His teeth showed as he snarled at the weird boy. ‘I just saved you life, kid!’ Feeling like the boy was nothing but an ungrateful little shit, Toothless decided he didn’t care much for that guy.

"Well, Toothless and I can help you look for it." Hiccup smile at the boy in an attempt to get his spirits up.

Jack turned with a broad slightly crooked smile too quickly. He lost his footing again and ended up falling onto Hiccup, which only made Toothless grow angrier. The dragon’s eyes slit as Jack looked up. He was now in Hiccups awkward grasp. 

"Umm?" Hiccup wrapped his arms around the other boy in an attempt to stabilize him. "Are you all right?" He helped the boy sit up beside him, sitting up himself he noticed Toothless on the defensive so Hiccup outstretched his hand to the Dragon. "it's okay buddy, he didn't mean any harm." Looking back at the boy Hiccup smiled again. "I'm Hiccup, what your name?"

Toothless huffed and sat with his back arched like an angry cat.

Jack felt a twinge of embarrassment. Usually he was more slick than this. “Jack Frost.” Then he looked at Hiccup again with a strange expression that left one eyebrow higher than the other. “Hiccup…” he smiled a little. “That’s a weird name.”

Hiccup pursed his lips and crossed his arms. "Oh and Jack Frost isn't?" Hiccup stood and walked closer to Toothless. Rubbing the dragon's head always seemed to help him calm down so he pet his dear friend as he watch the 'Jack' boy.

All at once Jack was back on the panic. “My staff! I have to go get it!”

Toothless growled. ‘Can’t we just leave him?’ The cocky dragon whined at Hiccup making a face that said he wasn’t fond of being near Jack.

Hiccup was once again confused by this Jack character. He couldn't seem to stay focused or stand, but he had been flying earlier. "What is it about your staff? That what you keep calling it, right? Why is it so important?"

Toothless nudged Hiccup on to his back. He was tired of dealing with this weird boy. He took off around Jack, glaring at him before he lifted into the air. Hiccup struggled against Toothless trying to get the dragon to turn around, but Toothless was would have none of it. He had decided it was time to head back to Stoick the Vast and the rest of Berk, even Hiccup would resent him a little for it. 

Flying higher and higher into the sky, Toothless tried to find the lights that had brought them there in the first place, but there was nothing as far as the eye could see. The dragon growled deep in his throat and swung around. Nothing here. Nothing there. There weren’t any ribbons of rainbow light anywhere.

They were trapped.


	2. Caution! Thin Ice!

**Summary for the Chapter:**

> After Toothless fails to find a way home, Hiccup insists of finding the strange white haired boy he just met. Though, flying after a winter spirit like Jack through dense woods can cause some problems. Frost has to save Hiccup's life from a too-familiar and dangerous circumstance _with out his staff!_

**Notes for the Chapter:**

> We weren't really sure were to take it, so we went with this cute cliche idea of Jack saving Hiccup and gaining Toothless' respect.
> 
> Enjoy!

The daredevil dragon that had attempted to find his way back home was blocked by one simple thing, the waves of light that had somehow transported his ride and himself to this other place were gone. Toothless growled and whined and flew quickly in one direction then the other trying to find some remnants of the aurora but had no luck. Finally, after many minutes of dragging Hiccup around on his back and taking him on quite an unexpected ride, Toothless just started gliding with an expression of disbelief on his face. 

Needless to say, Jack was very put off by the strange display. He watched as the two odd individuals took off into the sky. He was curious about them and he was looking forward to learning more about them, but it seemed that the giant winged lizard had a mind of his own. Jack remembered stories about dragons and such, but he hadn’t actually ever seen one; and that boy with the fuzzy vest and shoes was quite the sight himself. Jack noted the experience but then decided it would be best to forget about it for now and go get his staff. So, after figuring out his footing, he began to race back down the hill, into the woods, and started his search.

Hiccup pet Toothless' side confused by his friend's sudden out burst. But, since it appeared they wouldn't be getting back home tonight, Hiccup turned his friend back to the hill they left Jack on. Maybe, just maybe, the strange Boy could help him find a way home; or if nothing else, a place to stay while he tried to figure things out.

As they neared the hill Hiccup noticed that Jack wasn't standing there anymore. Quickly, he began scanning the surrounding tree line until finally, there at the bottom of the hill; Jack was spotted disappearing into the trees. Hiccup leaned into Toothless and they dropped closer to the ground. They began the tight swirling dance to avoid trees as Hiccup tried to locate Jack.

Jack was fast on his feet even without his staff. He knew these woods like the back of his hand. The problem was, he realized as he dashed through the plethora of trees, that he couldn’t jump or fly up very high and there was a good chance his staff was caught up in one of the trees. Still, he had seen the general area where his tool had fallen. He would start searching that area first. 

Hiccup caught a glimpse of white and blue dashing about to his right and turned Toothless in that direction.' Yes! There he is.' Hiccup Changed Direction again. "How is he moving so fast?" he asked the chilly air as he turned Toothless once again. 

Finally they were only a small distance between them, so Hiccup yelled out in hopes of slowing Jack down. "Jack!"

Jack stopped and turned toward the noise. ‘That kid again?’ He saw the boy on top of his dragon. ‘Yup.’ He stopped and waited for the two to land. He crossed his arms and leaned slightly to one side. Once again, he took note of how strange it felt to be without his staff. 

Toothless landed gracefully in front of the white haired weirdo and gave a huff. The hot air from his chest rolled over the stranger’s face and caused his hair to puff up for a moment. He smelt strange, like ice. But not like a human on ice, just like icy and that smell of when a strong cold winter wind comes in from the north. It wasn’t normal and it upset the dragon.

"Jack," Hiccup started. He smiled at the odd way the other boy stood. "Umm, right. So, it seem I can't get home at the moment. So I was wondering if you might be, umm, able to help us out." Hiccup looked at Jack hopeful then quickly added. "We'll help you look for your staff!" He hoped he could persuade the other boy to help him, other wise he would be very lost.  
Jack mused over the boy’s clothing that reminded him of a different era. He watched as the kid swung his arms back and forth as he spoke while rocking on his heels. ‘What an interesting character,’ he thought. He turned his head slightly, “You can’t find your way home?”

Toothless leered at Jack and the boy finally looked back. When they made eye contact the dragon began to snarl. 

Hiccup turned to Toothless unsure how to take his Dragon's reaction to Jack. As far as Hiccup could tell there was nothing worrying about Jack. Hiccup reached out and scratched under toothless' chin hoping it would sooth him. He turned back to Jack who was still staring at Toothless. 

"Umm, yeah. The lights are gone and I don't recognize anything in this area..." Hiccup bit his bottom lip as he shrugged his shoulders letting his words drift into silence.  
The dragon was unable to keep his senses when Hiccup began scratching the good spot. He instantly felt more at ease and began to purr. ‘It isn’t fair! Too. Good.’ Toothless began to purr and his body lowered.

Jack watched this scene with an amused smirk. “I’m not sure what lights you’re talking about, but sure. Help me find my staff, I’ll help you find your way home.” 

Since Pitch’s defeat, Jack had been spending a lot of time the same way he used to: frosting things over, playing tricks on unsuspecting humans, and otherwise wasting time. The only new factor was the extra time he spent tricking Jamie and leaving small things behind for the boy to find. Other than that though, he had to admit he had been growing more eager for something new and exciting to happen. So, between the idea of another adventure and the fact he needed some help finding his staff, he thought there was no point in not agreeing to the arrangement.

Hiccup smiled brightly as Jack's agreement to help him. He mounted Toothless and stretched out his hand to Jack. "So did it fall around here?"

Jack made a questioning face at the hand that was being offered. He then smiled and took it daringly. “Yeah. I’m pretty sure it fell around here.” He allowed Hiccup to pull him up onto the dragon’s back. He had to admit, to himself at least, that this was an incredible opportunity. He mounted the steed and looked over Hiccup’s shoulder at the dragon’s head. “You sure he’s friendly?” he teased.

Toothless looked back at the playful boy and growled. ‘Great Odin! Why are your feet so cold!?’ He looked up to Hiccup and whined. ‘His feet are freezing! Get him off.’ 

Hiccup smiled at Jack. "Yep, just a little nervous. From being away from home I think." He turned forward again and squeezing toothless' ribs with his knees and adjusted the tail flap for take off. "Lets go!"

Toothless turned back forward and made a very unamused expression. Once again, his human was ignoring him. Fine. They wanted sticks? He’d give them sticks. 

Jack was holding on loosely at first, but as soon as the dragon shot off he had to wrap his arms around Hiccups waist. It was all he could do to keep from falling off the beast. The sensation was weird for the young guardian because it had never really been an issue before. He found he felt very vulnerable without his staff and it sent small chills down his back.  
Memories of when Pitch had taken the staff and broken it returned. He thought he had lost it then. He didn’t want to feel that helpless again.

“Whow!” His attention was brought back to the there and now as the trees became suddenly too close. “What’s going on?” Jack raised one hand to block the raid of tree limbs that they appeared to be soaring through.

Toothless had shot forward then made his way up into the canopy. He was practiced enough to dodge the mass of branches in part because of their wide spacing in the strange little wood. He was also trained enough with his rider to know how to make sure that the individuals on his back meet face to face with various elements as he passed them. The dragon grinned as he heard the small pained complaints of the cold child on his back.

Hiccup shivered as Jack’s arms wrapped around him, but he didn't have time to think about how cold the other boy was as a tree branch smacked into his face. "Oww!" Jack asked him what was happening and Hiccup really couldn't tell him. "Toothless, Stop!, Oww!" Hiccup puled an arm up to block the next branch from making direct contact with is face. Once that was out of the way, he reached behind him and pulled Jack closer to his back leaning in close to Toothless. Making it harder for the dragon to hit them without hitting himself. "Toothless, Stop this! Get us out of here." Hiccup shifted his foot and changed the angle of the tail causing the dragon to divert sharply or run head first into a tree.

Toothless let out a small howl as he dodged the tree; the three of them came crashing down to the ground. The dragon rolled away from his passengers and managed to hit his head on a rock. He sat up dazed and wobbled about. Then, regaining some sense, he lowered his head and held it with his huge paws and cried. 

Jack rolled and slid over a large sheet of ice that covered a familiar pond. Fall had guaranteed the thin sheet of ice that crept over the water’s surface at night, but it wasn’t strong enough to carry much for very long. Luckily, Jack’s body automatically hardened the area hit struck so that he just bounced once then slid. “Owww… That was not the most fun I’ve ever had.”

Hiccup smacked his head against the ice as he separated from Toothless. Sliding to a stop he reached up and cradled his head. He suddenly stilled as he heard the ice beneath him begin to creak and crack. Hiccup tried to locate which way would get him onto solid ground, but he seemed to be very close to the dead center of the pond. 

The ice groaned under his weight. He slowly rolled onto his back and tried to ease away from the sound, but each movement only made the noises come quicker as more cracks sprang up. "Tooth- Toothless!" he glanced over at his dragon as the ice made and eerily ominous sound. He glanced over in time to see the ice beginning to brake through to water. "TOOTHLESS!"

Hearing the call of his friend, Toothless jumped to his feet and dashed to the edge of the pond. He yelled out a loud, desperate growl at the boy, but he didn’t dare step on the ice. He opened his wings to fly over and grab the boy but there wasn’t enough space for them to open fully. Toothless started shifting from paw to paw in anxious irritability. He growled out another call, ‘Hiccup! Hold on! I’ll think of something! Don’t move!’

Jack’s eyes opened wide and he turned to see a very unforgiving sight. “Hiccup! Don’t move!” Jack got to his feet. “Don’t move an inch! I’m coming!” 

Hiccup tried to shift closer to Toothless as the dragon growled his concern. The ice shifted under him and he panicked trying to get off the crumpling surface. Jake called out to him and Hiccup snapped his eyes on the white haired boy. Hiccup stilled, amazed at how Jack seemed to glide over the ice as easily as he would walk over the grassy hills of Berk. The ice shifted once again and hiccups pulled his feet closer to himself.

Jack reached out a hand as he danced almost effortlessly on the ice. He wasn’t sure how he was freezing the ground without his staff, but it didn’t matter right now. He moved closer and closer to Hiccup and as he did so, the ice stiffened. “Alright. Now, just stay still and I’ll get you.” His voice was much calmer now. He had a soft smile on his face. “I won’t let anything happen to you. I promise.”

Toothless watched in amazement as the strange boy moved to hiccup’s side. He licked his dragony lips as he watched Jack get down on one knee, touch the ice near Hiccup with one hand, and reach out with the other. 

“Grab my hand, Hiccup.”

Hiccup instantly took the hand and nearly jumped onto Jack, fearful of falling though into the freezing water. Jack just seemed to glide along unfazed by the treacherous ground beneath him. Whatever this boy was doing seemed to be working and he could question it later; as soon as he was on solid ground. -But for now Hiccup just wanted off this pond.

Jack grabbed hold of Hiccup’s arm and tugged him over to the thicker side of the pound just at the ground gave way under him. He managed to pull the boy next to him with relative ease and once he realized they were fairly safe, he let out a long sigh.

Toothless stared wide eyed until he was certain Hiccup was safe. Then the dragon let out a loud sigh and fell onto his side. ‘Good gods….’

Hiccup latched his arms around Jack. He was having a hard time standing on the ice. His metal foot kept slipping on the slick surface. Hiccup let out a sigh of relief himself before shivering. Jack was almost as cold as the pond they stood on. "Thanks." Hiccup didn't let go of the other boy fearing he would fall the moment he did.

Jack laughed and helped keep Hiccup upright. For the first time, he noticed the boy’s disfigurement as it made things even more difficult for the kid. “So,” his voice held the hint of childish teasing. “You two aren’t from around here, huh?”

"Humph, like you couldn’t tell already." Hiccup tried to take a step forward hoping Jack would get the hint and slipped. It looked like he was dancing about like a newborn fawn for a moment. Once stabilized, he smiled crookedly up at Jack. "Umm, I'm from Berk. What do you call this place?"

Jack helped the boy off the ice with slow coaxing. As he did so, he spoke playfully. “Name of the place? You mean like the town? Or the name of the woods? Or the country?” He was mostly teasing now as he got Hiccup to safety. 

As soon as the two were off the ice, Toothless was rushing around the pond to be at Hiccup’s side. He got there in only a few bounds and placed his face against Hiccup’s body and purred.

Hiccup narrowed his eyes as Jack playfully avoided answering his question. Stepping onto solid ground, Jack let him go just in time for Toothless to nudge his head against Hiccup. Hiccup smiled as he wrapped his arms around Toothless' face. Toothless’ purring made him giggle as it rumbled through his body. "I’m all right buddy, nothing to worry about." Toothless lifted his head slightly lifting Hiccup into the air a bit making him laugh harder.

Jack watched and smiled warmly at the scene. What a cute couple the two were, he thought. The two of them seemed to be quite the impressive team. “So, what exactly is that big guy?” He decided conversation was in order and he was dying to know.

Hiccup turned to look at the other boy and signaled for Toothless to put him down with his hand. Once standing on his own two feet, he turned to Jack while his hand continued patting Toothless' head. "This is Toothless. He's a Nightfury. Only one we know of back on Berk." He turned back to Toothless. "One of a kind, aren't we buddy." He smiled, scratching under Toothless' chin once again.

“A Nightfury? Right. Yeah. And that would make him… some subspecies of… lizard?” 

Toothless went from purring to huffing. ‘Lizard!? Lizard!?’

Hiccup looked confused for a moment. "No a dragon. Don't you have dragons here?'

“Dragons! Here? Haha!” He laughed for a moment then gave a very serious expression and a sturdy, “No.”

Toothless’s mouth dropped open. ‘No dragons? How can you not know what a dragon is?’ He looked from Jack to Hiccup then back and forth again. ‘What’s with this guy?’ He gave a slightly confused growling noise.

"Really?" Hiccup couldn't believe his ears. He'd never heard of a place without dragons. Suddenly he feared for Toothless' safety. What if the people tried to hurt him or take him? Hiccup stepped closer to Toothless defensively.

“Alright!” He brushed passed the dragon talk for now and focused again. “This is cool and all, but I really would feel better talking about this with my staff in hand.” His cocky attitude was still nicer than most of the manners of anyone in Berk, but Jack still had a way with moving from one subject to his own pretty securely. 

"Ah! Right" Hiccup mounted toothless again and once again outreached his hand to Jack.

“I think I’ll walk this time if it’s all the same.” Jack didn’t want to relive that last experience.

Toothless purred and gained Jack’s attention. Then, he lowered his head and gave a small gesture towards his back. Jack Frost had saved Hiccup. That was enough to him.

Hiccup understood Jack’s trepidation Toothless had been quite unreasonable, but the dragon seemed much calmer now. "Ah, yeah. It won’t happen again. I promise." Jack looked at him for a moment so Hiccup continued. "We both promise." Hiccup wiggled his fingers in a 'come on' gesture.

Jack wasn’t much of a coward and the dragon did seem to have warmed up to him. “Alright.” He grinned and grabbed a hold of Hiccup’s hand.

Toothless smiled as his rider brought the second boy aboard. He was much more content to fly with Jack this time and he decided that he wanted to help the boy find his stick. ‘Though I have no idea why it’s so important to him.’

Hiccup once again noted how cold Jack's arms were as they took to the sky, much calmer now. "So what's so important about this staff of yours?" He asked over his shoulder as they glided throw the treetops.

“It’s mine,” Jack said simply. “It’s a part of me.” 

Toothless chirped in confusion by that statement.

Hiccup glanced over his shoulder and an eyebrow raised. "O-kay." He face forward again rolling his eyes. "Can you describe it to me, I only saw a quick glance of it before."

“It’s long. About one and a half Hiccups tall.” He smirked at his own commentary. “It looks kind of twisted. And has a larger bulb like base at the top.”

‘So… it’s a big stick?’ Toothless sighed and kept searching for anything that seemed out of the ordinary. 

Hiccup rolled his eyes at the comment about his height. "All right, lets see what we can find?" Hiccup slowed Toothless down just a bit and began searching each of the branches they flew past.

Jack and Toothless both looked for any sign of the missing object. Occasionally Jack would suggest that they had traveled too far one way or another. They circled around for several minutes before Jack finally saw a section of branches that looked particularly disturbed. “There!”

Hiccup turned them in the direction Jack indicted. The branch cover was thicker there and Toothless had to take to leaping from branch to branch in order to get close to it.

Jack was enjoying the ride and let out a laugh as he rode the dragon down the many limbs of the tree. Then, he saw it, his staff. “There!” Toothless halted and tried to figure out which direction to go, but before he could manage anything Jack have already stood and leapt from his back. 

Hiccup panicked as Jack leapt from Toothless, they were very high and a fall from that height could easily kill the boy. Hiccup reached out to grab jack's arm but he was already out of reach.

Jack landed painfully on the branch nearest his staff. The impact wasn’t fun but he’d felt worse. He reached out before he fell to the next branch and took hold of his staff. As soon as the object was back in his hands, he shot up and stood on the branch effortlessly. 

Toothless stared wide mouthed down at the boy who had just levitated back into a standing position on a tree branch that should be breaking under his weight.

Frost was grinning ear to ear and his mouth parted as he sighed. He held his staff out and looked it over. It was fine. He laughed and swung it once in front of him then put it at his side where it belonged. He looked up and waved to his new friends. He pointed at his stick and said pleasantly, “Got it!”

**Notes for the Chapter:**

> Thank you for reading this far in. So, we haven't made too much more of this one. (Chapter three isn't finished at all.) We have Hiccup being introduced to Jack's world a little, but not much more.
> 
> If you like the story thus far and would like to see more, let us know by leaving a comment. Would you guys like to see Jack/Hiccup cuteness? Hiccup/Toothless? Let us know! :)


	3. Excersize is a Great Way to Bond.

**Summary for the Chapter:**

> Toothless and Hiccup decide to play around with Jack. They end up in the middle of a human street where things get complicated. The two outsiders finally realize the base truth of Jack and his world, but it doesn't turn them off any. The three decide to be good friends while they look for a way back to Berk and the rest of the pair's world. 
> 
> Jack get addicted to the fun of his new friends and contemplates keeping their way home a secret for the sake of more fun.

**Notes for the Chapter:**

> Hey guys! Thanks for continuing the story. 
> 
> This one was quite a bit longer and filled with a lot of character exposition, but we hope you don't mind. They're relationships are building and soon, some interesting things will be happening.

Hiccup stared at Jack in disbelief his mouth hanging just open. "You, you just flew. How is that possible?"

Jack laughed and decided to show off a little. “Catch me and I’ll tell you.” With that, the white haired boy shot off the branch and took off into the air with a cold black of icy wind propelling him.

Toothless stared jaw dropped. ‘What in the world just happened? Humans can’t fly! Can humans fly? No! How is he flying!?’

Hiccup watched him, still startled for a moment, then urged Toothless into the sky. They darted after the swirling whirlwind that Jack Frost had become. Hiccup soon found himself caught up in the chase and was laughing as they almost managed to catch Jack, but the other boy was wiry and spun just out of reach time and again.

Becoming more determined, Hiccup leaned into Toothless making them more aerodynamic and shifted his foot. They shot up to Jack and took a sharp turn around him so that he was pressed into Hiccup's arms. Hiccup smirked triumphant into Jack's startled face.

Jack laughed aloud and complimented the two in their effort. “No one’s ever caught me before!” He was trilled beyond words. Fun was Jack’s game and these two had just made the game very interesting.  
Toothless growled a happy sound and looked over to Jack. He smiled and Jack noticed why the dragon was named Toothless. ‘Pretty impressive, kid. But you’ll never been me.’ 

"Oh is that right?" Hiccup laughed. "Well I just did,” he boasted proudly on the back of his awesome dragon. “So, you have to tell me how you can fly now."

Jack laughed and flew out of Hiccups grasp. He turned himself onto his back and seemed to relax in the air. “The wind.” His answer was very simple. “It carried me.”

"The Wind?" Hiccup paused for a moment. "The wind carries you?" He stared at Jack, an eyebrow raised.

“Yeah.” Jack held his hand out and called the wind to his fingertips. “My staff allows me to summon it.” His fist tightened around his staff’s midsection. 

Toothless let out a snort. That was the most peculiar thing he had ever heard. 

Hiccup narrowed his eyes at Jack, he felt as if Jack was having a joke at his expense. "Right you can summon the wind but you have never seen a dragon before." Hiccup crossed his arms over his chest. "If you don't want to tell me that you could have just said so." Leaning over Hiccup pets Toothless' head. "Let’s settle for the night buddy, what do you say?" 

Hiccup and Toothless turn from Jack and head back for the hill they had first landed on.

Jack kept floating on for a moment, and then turned. “H-hey! Where are you going?” He caught up with them easily and scoffed, “You think I’m lying? You can see me, and you are riding a dragon, and you don’t think that Jack Frost can summon wind to help him travel?” 

Toothless listened but focused on safe flying as he did so. Then, something he hadn’t really noticed before caught his attention. There, on the land in front of him, were thousands of stars. Small orange, yellow, white, and bluish lights glistened in the near distance. It was beautiful and unlike anything he’d ever seen. Human huts, or something else human made he thought, were lining the road up ahead and they had colorful fires burning as bright as stars or the moon. The sight made the dragon chirp and click with awe.

Hiccup just watched jack as he spoke still disbelieving. "There you go with that again." He huffed as Jack finished. "Say I can see you like it's some crazy unheard of thing! Why wouldn't I be able to see you? You are right in front of me." Taking a deep frustrated breath he continued. "And of course I think your lying, humans can't control the wind, with a staff or not. The wind belongs to the Gods."

“H-human?” Jack laughed in disbelief as he straightened out. “I don’t want to burst your bubble, but I’m not human. I’m a-“ then he paused and quirked an eyebrow. His smile quirked and stuck only on one side as he tiled his head suspiciously and asked, “Wait a minute, how can you see me if you don’t know who or what I am?”

"Because you ARE RIGHT IN FRONT of me!" Hiccup nearly screamed with frustration. He was beginning to think Jack was insane or a figment of his deranged mind. Maybe he and Toothless had flown to high and ran out of oxygen and were now plummeting to their deaths and this was just some strange test Odin was asking him to past so that he could get into Valhalla.

Jack could sense the tense emotions pulsating off of Hiccup. “Jeeze, relax, kid. It is kind of a big deal around here for people to see a guardian is all. Usually they have to believe in me first. And that usually involves knowing who I am.” He rolled his eyes and shook his head in a mock-disapproving way. 

Toothless started to fly towards the human town without Hiccup’s acknowledgment. He purrs loudly as he got closer to the brilliant scene.

Hiccup watched jack for a moment before responding. "A guardian? You watch over something? Who would trust you with any thing? You can't eve keep a hold on your stick." Hiccupped finally noticed the brightness Toothless was heading for. He squinted trying to recognize any of the shapes or objects they where flying toward. "What is that?"

Jack’s carefree expression turned a bit sour. ‘Who would trust me with-… …-my stick?’ He was about to say something snide when he noticed that his two new connections were busy staring wide eyed at the town. 

“What’s what?” He looked. Nothing seemed to be out of the ordinary. He looked harder just in case. Still nothing. “I don’t see anything.”

"How can you not see it, it's huge." Hiccup motioned at the town.

Jack cocked his head then flew out in front of them. He had to fly quickly backwards at first to keep from melding faces with the dragon, but after Toothless’ initial panic reaction of being so suddenly distracted the Nightfury slowed his charge and landed down below where he was led by Jack. 

Toothless growled and Jack patted him on the nose then flew up and hung over Hiccups head. “Alright. You are too weird. You have a dragon. You can see me but don’t know who I am. And you don’t know what a town is?”

"This is a town! How..." Hiccup turned from Jack to the town. "How do you make so many different colored fires? Are those you homes?" Hiccup dismounted and walked closer to the town gesturing at the buildings. "What do you call those?" Hiccup pointed at a mail box." He rushed forward, jumping up to point at a streetlight. "How do you do this?" He turns back to Jack his eyes alight with the prospect of new knowledge.

Jack cocked his head and hugged his staff. He began to answer all of Hiccup’s questions with a very amused smirk playing on his lips. This boy—who was riding a dragon for Pete’s sake—knew absolutely nothing about the normal world. How is that possible, he wondered.

Toothless was just as curious about the new world. He began to sniff at, paw at, lick, and otherwise examine everything he came across. As the dragon padded through the street, Jack began to wonder if they were flesh or spirit. He figured he’d find out soon enough as a car turned the corner and moved in their direction. 

Hiccup turned at the strange sound of an engine grew closer to him. Tilting his head to the side, he watched the strange thing approach. "Jack? What is this?" Hiccup pointed in the direction of the car as he turned back to Jack. Brakes began to squeal as the car attempted to slow, but it was to late. The bumper slammed into to the back of Hiccup's knees sending the boy into the air. Hiccup let of a sound of pain as the ground was pulled away from him.

Jack had realized just a little too late that at least Hiccup was visible, which meant that he could be hurt. The icemaker rushed forward and swept Hiccup from danger just as the car made its first contact. Jack swore he heard something break before he could fly the boy to a safer place. When he sat Hiccup down off in the tree line, he began to check him over desperately. 

“Are you alright?” He felt awful for allowing this to happen. Of course, that would only last as long as he wasn’t certain of Hiccup’s condition. “That car hit you. I heard it. That sounded bad.”

Hiccup curled up with his legs against his chest, rubbing at the already forming bruises. It hurt a lot, but he was fairly certain that he had not broken anything. The back of his head hurt quite a bit as well but he wasn't really sure why. He didn't recall anything hitting it—though in all honesty he was unsure how he had gotten where he was now. He blinked and swatted at the frantic movements of Jack. He felt dizzy and the way Jack was moving wasn't helping at all. Then he registered the other boy had said something: a word he did not know. "Car?" he grabbed Jack's arm to still him. "What’s a car?"

A loud honk and terrible grounding noise ripped out through the night back on the street. There was a sound the dragon rider could recognize as his steed’s charge. Then, the sound of the Nightfury’s blast mad Jack turn back. “Oh no.”

Toothless had scene the strange creature attack his beloved human and it infuriated him. He ran up on the beast and roared threateningly. Then, a human who had must have been the beast’s last meal screamed inside of the monster’s assumed translucent stomach. The dragon smashed down on the metallic thing’s supposed mouth and dropped back when it began to make a terrible honking sound. As a last effort to scare the thing off, Toothless dropped his head, charged his blast, and fired it at the creature’s face. 

Hiccup pushed Jack out of his sightline and watched with wide uncertain eyes as Toothless destroyed the 'car'. A person burst out of the side of the thing and ran from Toothless and the car. Hiccup swallowed his stomach back down and shouted, "Toothless!"

Hiccup fumbled back to the ground as his sore legs protested the effort, but he forced himself to stand again. He ran as best he could for his growling dragon. The blackened car was making an odd sound like dripping water as well as the crackling of firewood and it sent uneasiness through the young Viking. A moment later, the car exploded knocking Hiccup to the ground once again. Hiccup shielded his face with his arms as Toothless tumbled backward over himself away from the now charred burning pile of metal. Peaking through his fingers Hiccup gasped at the mess in front of him. Then glanced franticly until he spotted Toothless father up the road.

Toothless snarled at the thing that had attacked him, then threw up the human it had inside, then tried to fight back. The Nightfury figured that whatever the beast was, it worked kind of like a dragon. If you hit it just the right way it would blow up from the inside. He jabbed at the lifeless form of the modern vehicle with a swift punch from one of his paws. When he was certain it was dead, he smiled proudly and turned to Hiccup with an expression of pure pleasure. He’d killed the monster stupid enough to mess with him and his rider.

Jack watched the human run screaming from her car. His face met with his palm. As he peeked through he cracks in his fingers, he noticed that people in their houses where now leaving their homes to gawk at whatever had just occurred in their neighborhood street. “Oh no.”

Frost rushed from his spot and, with a gust of cold wind propelling him forward, scooped up Hiccup and tugged on Toothless’ face. “Come on! We need to go! Now. You’re physical!”

"Physical?" Hiccup asked, allowing himself to be lifted into the air. "Of course I'm physical. I am person, aren't I" Reaching out he pet Tooothless' head and the dragon followed the boys higher into the air.

Jack led the two out a ways from civilization and hid them in the deepest section of the woods. It was dark there, save for the light of the nearly full moon that rested overhead. After landing, Frost took a deep breath then let it out in a nervous and amused laugh. “Whoow! So, that was fun.” He looked over to the two very confused travelers and sighed. With one eyebrow raised and a sassy tone in his voice, “You really don’t know anything about the world, huh?”

Toothless growled, “What do you think you’re saying? What the heck was that thing!? Why didn’t you warn us about that thing?”

Jack leaned on his staff, ignoring the dragon once again. “Look, I’m Jack Frost. I’m a winter spirit. Humans can’t normally see me. Once children of the world that believe in me could see me, and even then it isn’t like I go showing off to them. And that’s only possible because I’m a Guardian. But you two, even the dragon, can be seen by humans. That’s kind of weird. Got it?”

Hiccup leaned against Toothless' shoulder. "So people don't normally see you and you guard something." He nodded slowly then hooped up on to Toothless' back, his legs were still sore and standing wasn't helping them any. "So a few quick questions, Spirit: What was that thing? Why did it try to kill us? And how can you guard something if no one can see you?"

Toothless snorted in agreement. Those were all very good questions.

Jack laughed. “Alright, well I’m a guardian of children. I fight the creatures of darkness and stuff whenever they pop up. I bring the fun, and they stay happy.” He stood straight and began to play around with his staff, swinging it back and forth carefully. “That ‘thing’ was a car. It wasn’t trying to kill you, and neither was the person inside of it. Humans like to use cars now a days to travel. It’s why they built them. It’s faster than walking and unlike us they can’t fly. No winter powers. No dragon.”

Toothless looked back at Hiccup with pleading eyes. “Is this guy serious? Are we just going to listen to this?”

“You know, cars are like….” He paused for a moment and thought. “Boats or planes, but on the ground. They’re not alive. They’re just contraptions people use to get from place to place.” He wasn’t sure the two strangers would know what a boat or plane was, but he was hoping it might ring a bell or two.

Hiccup nodded slowly. "Okay, so it's a land boat. Got that. Don't know what a plane is, but we'll just let that go for now." Hiccup leaned down and popped his shoulders. "So what creatures of darkness? And don't the children fight along side their parents? We Vikings carry weapons as soon as we can lift them." He plopped his head in to his hands atop Toothless’ head and raised an eyebrow at the white haired spirit-boy.

“Fight with their parents?” Jack’s face twisted with amusement. Some pearly white teeth showed as he half smirked at Hiccup as he tilted his head to the side. “Not around these parts. Parents can’t see the shadows, or anything else for that matter. And kids can’t defend themselves with anything but good thoughts. Which, it just so happens, is part of the Guardian’s work: to keep them in high and youthful spirits.”

Toothless wondered for a moment if all human adults in this world were blind. One hit him with their land boat, and others couldn’t see the dangers going after their offspring. This sounded ridiculous. He shook his head with a sigh of disbelief. 

“And, uh, Vikings. That’s cool. A little before my time but I’ve seen relics of the Vikings.” Jack jumped up onto the top-most tip of his stick and looked down at Hiccup with a teasing smile.

Hiccup cocked his head to the side to watch Jack. "Before your time? We're a thriving people, what do you mean before your time?" Hiccup absent mindedly rubbed at the sore spot on his leg.

“Hmm? Well,” Jack put a finger to his lip and thought. “To the best of my knowledge, Vikings haven’t been around for a few hundred years. Last of them died out before I started exploring the globe. “ 

Toothless’ mouth dropped open. His gums glistened in the moonlight along with his reflective eye lenses as he stared dumbfounded at the white haired boy who was claiming something that, once again, sounded completely preposterous. 

“Oh well. As far as I knew, dragons weren’t real either. And all the major cities of the world have electricity and cars. Even poorer countries have knowledge about them. So,” he placed both hands near his feet on the staff’s tip. “I suppose you are from a world where history doesn’t really matter. I bet you he would know.”

With uneasy curiosity, the Nightfury followed Jack’s gaze up to the large round orb in the sky behind them. “The moon?” he growled. “How would the moon know anything?”

Hiccup's chin slid off his hand and gapped open. 'Gone! Gone! How are the Vikings gone!' he screamed inwardly. Slowly turning to follow Jack's eye line, he saw the moon starring back at him. "Your moon talks?" Hiccup sat up right. "This whole place is strange. I just want to head back. My father will be looking for me. I have the academy to run. Just tell me how to get back to the auroras and get me home."

“Sorry there, dragon rider. The moon doesn’t say much at all, even when he should. And I don’t know anything about world transporting auroras.” Jack allowed one foot to swing down as his pose relaxed. He felt bad, not being able to help his new friend. He decided he had to lighten the mood. “So, academy huh? You look a little young to run your own school. What do you teach?”

Toothless padded impatiently. “This guy is no use,” he whined. “Let’s go Hiccup! We need to find a way home.”

A bright smile bloomed on Hiccup’s face. "Yes well, I might be young but I was the one who figured out how to train the dragons in the first place." He puffed out his chest proudly. "And, well, to make a long story short, after that my father turned the Dragon hunting arena into the Dragon training academy. Right now I'm pretty much teaching the whole village who to live with the dragons. Well along with Astrid, Fishlegs Snotlout and the twins, Ruffnut and Tuffnut."

Hiccup nodded quite proud of himself.

Toothless seemed proud of his rider too and gave a small chirp of approval. 

Jack, on the other hand, found that all of this information—including the strange names—was more than just a little odd. He couldn’t help but laugh, “Does everyone have such strange names where you come from?”

Toothless growled and Hiccup was about to defend and explain yet another aspect of his culture when Jack had decided that enough was enough for now. A snowball had smacked Toothless right between the eyes. The dragon made a startled sound and shook the chill from his face. He then looked at Jack who was standing proudly with another ball at the ready. His irises grew suddenly very thin as his eyes dilated. The instinct to play was stronger than normal. His pupils narrowed slightly and he bent down in a playful position that warned he might pounce.

Jack smiled and tossed his extra snowball at Hiccup. It smacked the boy in the face. Frost watched in high hopes for the relaxed fun he was certain would start soon. 

Hiccup was knocked backward slightly by the impact. Deciding that he would use this to his advantage, he slid off the side of Toothless. Immediately flipping onto his feet, he scooped up a hand full of snow, popped up from behind the dragon, and tossed the snowball at where Jack had been only to realize he wasn’t there anymore. 

“Ooo!” Jack’s voice came from above and behind Hiccup and Toothless. Jack was floating in the air and hair another two snowballs at the ready. “You missed me by just thi-s much.” He grinned mischievously and pinched his fingers together to show size.

Toothless half growled-half purred and tried to swat Jack with is tail to no avail. Jack dodged and threw another snowball in the dragons face. Toothless shook it off and looked at Hiccup and growled, “Wanna team up? Lets get him.”

Hiccup ducked away from the snowball aimed for his face and grabbed another from the ground. Making sure to spot Jack first this time, he let the ball fly. Scooping down to form another before seeing if that one makes contact, Hiccup laughed and rolled under Toothless' legs to make him self a more difficult target.

Toothless began to nuzzle the ground and moved away from his rider as he rolled up his own ball of chill. With Hiccup out in the open, Jack decided to strike back. Three balls later, Hiccup was covered in small patches of frosted water. 

Hiccup threw the ball in his hand and laughed knocking the snow from his head, shoulders, and chest. He shook his head trying to get the last of the snow from his hair. He watched Jack flip out of the way as a large blob of snow flew threw the air nearly hitting him. Hiccup laughed again grabbing some snow and lunged at the other boy. Managing to catch him off guard, Hiccup dumped the snow down the front of Jack's shirt then dropped back to the ground

Jack’s eyes grew wide as the snow met his skin. The sensation was exciting. He rarely got to play directly with children; even now that he was a guardian he was not aloud to interact with them. It was an immense thrill to be a part of the game so completely. He laughed and waved his staff over the ground to make dozens of small balls for the quick grab. 

It didn’t take long for Hiccup to discover the ammunition, or for toothless to get the idea to use the premade ones to make bigger ones. Snowball after snowball was rolled and tossed around. By the end, everyone was covered in white dust and frost flakes. It had started snowing half way through the game and all three boys were having fun and laughing so hard their bellies hurt. 

Jack finally surrendered when Toothless had pinned him under his massive paw and Hiccup had threatened him with the final attack.

Hiccup nodded smugly at Jack's surrender but still threw the last ball in the winter sprit’s face with a triumphant laugh as he high-fived Toothless' paw. "Great job Bud! He never stood a chance." Hiccup placed his fist on his hips and smiled down at Jack.

Jack smiled up at his two new friends. They were fun, a lot of fun. He hoped the moon would let them stay for a while before Santa or Sandy found them and tried to send them back to their world. Then a thought came to him, could Santa get them home with his orbs? Could he visit their world? The idea was entertaining. He would keep that idea on the backburner. For now, he wanted to play more and learn more about the two strangers. That couldn’t possibly hurt anything. He just had to keep them out of sight of the humans, and out of the other guardians’ radars.

**Notes for the Chapter:**

> Prepare for slash in the next couple chapters!  
> FrostedCup, ToothCup, and FrostedTooth are all possibilities! Keep an eye out and let us know what you think. <3


	4. When Jack's Away...

**Summary for the Chapter:**

> Jack leaves Toothless and Hiccup to go find something to help keep them warm. Toothless gets a few ideas on how best to warm his rider up. Hiccup gets a little to excited about the contact though and shares a more than awkward moment with his dragon.

**Notes for the Chapter:**

> Warning: This is a Toothless/Hiccup sexual scene!

Jack had spoken with his new friend Hiccup about all the many differences between their two worlds. Hiccup and Toothless marveled about the creations of this strange place and told of their own epic tales as Viking dragon rider and dragon. The three of them continued to discuss things like games and dangers and trees and ice for many hours before Hiccup finally stretched his arms above his head and gave a great yawn. 

After admitting that he was only human, and so needed sleep regularly, Hiccup was met with a very confused Frost for half a moment before the boy jumped up to his feet then off the ground entirely. “Follow me, I know a safe place big enough for you and gargantuan over there.”

Toothless gave a little growl at the statement, though he was now quite familiar and found of the white haired boy. Besides, he was a pretty big dragon and he was proud of that fact. He bent down and allowed his boy to get onboard. They followed the spirit boy through the forest to a cave hidden behind a very chilly, small waterfall in the heart of the woods. 

“How’s this? Warmer inside,” Jack assured the two visitors. He may not have a need for that sort of thing himself most of the time, but he was aware that places like that could be quite comfortable to rest in.

Toothless allowed Hiccup off his back and sniffed the air. It smelt safe and fairly clean. He wondered off with swag in his hips into the space behind the waterfall. Once he was sure it was all clear, he gave a pleased chirp and began rubbing on the stonewall to ease his itchy scales.

Hiccup ducked behind the falls and while his was warmer, it was still very cold and all the now melted snow that had settled on his clothing was beginning to make him shiver. He watched Toothless fight to get an itch just under the riding saddle. Hiccup stopped his friend and removed the offending piece. Toothless went back to scratching happily as Hiccup placed the thing on the ground and looked at it sideways for a long moment. With a nod to him self, Hiccup spun and flipped that saddle over several times until it lay exactly how he wanted it on its side. Then Hiccup lied down placing his head on it as though it were a pillow. Hiccup curled into a tight ball in an attempt to warm himself as he tried to get comfortable enough to sleep.

Jack looked the two and made a concerned face. Hiccup, at least, was cold. He thought to himself then snapped his fingers. I’ll go grab them some blankets. I can do that, he thought. With that notion, he jumped off into the night to find his new friends something warm to hide under.

Toothless had finished up with his scratching and had moved to hiccups side. He looked down at the little curled ball for a moment. Then he smiled and shook his head. “You’re soaked. You’ll get sick if you don’t get out of those wet things and warm up,” he growled. With that, he bent down and began tugging on Hiccup’s vest.

Hiccup looked at Toothless and sighed. "Well I don't have anything else to put on and standing around naked isn’t going to help me any." Toothless continued to tug on the vest. "Fine." Hiccup uncurled and let Toothless pull the vest free of him.

Toothless purred and then latched his mouth around the boy’s shirt next. He urged the boy to remove one article of clothing after another until Hiccup was sitting on the cold ground of the came completely naked. The boy’s dragon giggled with growls as his rider complained while he worked. Toothless scooped up all the clothing in his mouth, walked over to a section in the cave where he could place the clothing on top of a branch that hung broken inside of the cave, and used one of his signature blasts to heat the stone under the now hanging clothes. 

"You are ridicules. Now I’m cold and naked. Thank you, you stupid lizard" Hiccup grumbled as Toothless carried his clothes away. Hiccup shivers became more violent until, annoyed, he stood and walked over to Toothless. He crouched under the dragon and pressed his back to Toothless' chest, hopping to absorb some of his friend’s heat.

"I blame you for this" Hiccup shivered out.

Toothless looked down at the quivering Hiccup and smiled. He cocked his head while examining him, and then decided he should probably help warm the boy up. “Here,” he growled. His head lowed as he picked the boy up with his paws. Toothless sat back on his butt and sat Hiccup on his belly. Then, the dragon opened his mouth wide and breathed out hot air all over the human as if to defrost him. 

Hiccup wrinkled up his face as Toothless breathed on him. While he had been warmer momentarily, he wasn't so sure the fish breath was worth it. "Need to work on that breath of yours bud," Hiccup said turning in Toothless' paws so that his chest was pressed against the warmth. He could handle a cold back better than a cold font any day. Folding his arms in-between himself and Toothless he scrunched and unscrunched his fingers to get the blood flowing once again.

Toothless sighed. It seemed that hadn’t done the job. He decided to try something else. The large paw not under Hiccup’s rump began gently rubbing the boy’s back. It seemed to shake Hiccup more than warm him. Then, he pulled his rider back from his body and lifted him to his face. Once there, the Nightfury began to rub his nose into Hiccup’s belly. He made soft purrs that seeped out of his nostrils and forced hot air over the boy’s vulnerable body. The dragon nuzzled his human companion’s abdomen passionately. He made an effort to stroke every inch of the front of the boy in order to warm him up.

Hiccup giggled and wiggled against the sudden muzzle rubbing attack. He was indeed warmer; in fact parts of him seemed warmer than normal. A puff of warm air brushed against his genitals. Hiccups gasped and tried to wiggle free of Toothless. "Stop" He gaspingly giggled at the dragon, but it even sounded to playful to his own ears. When it happened again he dropped his head onto Toothless'. "Please Toothless, Stop." 

Hiccup quietly cursed how ticklish he was. His laughter was getting in his way now, and if this continued much longer he would have to attempt some unheard of acrobatics to hide his growing erection.  
A deep blush had settled on to his face and he squeaked as he felt Toothless take another pass. "Pu-put me down." Panic filled him and he began to wiggle frantically. "Put me down, Toothless... Aaah"

Toothless found the entire act very enjoyable. He could feel Hiccup’s body getting warmer and hearing him laugh was always a pleasure. The dragon took the wiggling around as a challenge to hold on tighter. It wasn’t unusual for them to play that sort of game. Nothing really seemed off to the larger male until his nose ventured too far down and bumped into something not quite familiar with a very familiar scent that filled his sinuses. 

Large pupils quickly shifted upward to look at the boy whose hands were pressing down on his dragon’s scaly head. Large green eyes stared up at Hiccup as his motions suddenly stopped. The dragon stared for a long moment before he began sniffing the tender lower belly of him comrade’s form. He was familiar with the scent but he had never been allowed inside the hut when Hiccup reeked of it. He was always told to go play somewhere else. Now, he understood why.

“Hiccup?” Toothless whined up at his rider without removing his dragony lips from Hiccup’s groin.

Hiccup squeaked and closed his eyes as Toothless looked up at him. Part of him wanted to run screaming, very much like he had done when his father was speaking with him earlier that day. Though, another part of him was extremely pleased with the way Toothless was pressed against him. As he really registered that thought, he groaned in frustration.

Toothless continued to stare up at Hiccup with his bright, big eyes. “Hiccup? Are you aroused?” he growled softly. He had to admit, he had never given the subject on human sexuality much thought. He knew that Hiccup was male, and that as a male he had an interest in a female from his clan. However, the thought of what the boy ever planned to do with his girlfriend was an entirely different matter. Now that he realized that incredible musk was Hiccup’s pheromone, Toothless was considering his options. 

Hiccup sighed heavily. He had been trying to will his erection down since Toothless spotted it but the soft growl sent an entirely different shiver running through him. Sliding his hand to rub between Toothless' eyes he whimpered, "Put me down." Odin help him, he didn't need those few late night dreams to have a chance to actually play out. He had been spending so much time with Astrid to stop them. He had thought it was working at first, he hadn’t had any dreams about the matter for several nights, but then they came back. What had started out as a nice day in the woods with Astrid somehow always turned into him pressed into the moss as Toothless took him while purring in his ear.

Hiccup had been sure something was wrong with him; that he was as much of a hiccup in this department as he was in almost every other Viking category. Stoick had unwittingly confirmed it was true earlier when he sat his son down to discus carrying on the family name. If Stoick ever knew the truth, Hiccup would either be killed or disowned or Toothless would be killed or sent away. Nothing good would happen. That was at least certain. 

Hiccup dropped his head to Toothless' again. Now that it was right in front of him, he wanted it; he wanted it desperately. Hiccup wrapped his arms around Toothless' head and almost sobbed his name.  
Toothless purred as he stared with a sense of worry for his friend. The boy seemed hurt or upset about something. He was going to pull Hiccup from his face because he thought maybe he was offending the human. Then, just as he pulled away, he felt his rider’s hardened prick quiver against his lip and heard his master’s voice break into an accidental moan. 

“Oh,” Toothless’ eyes turned down and he went a little cross-eyed as he tried to look at the human’s stiffey. He stared for a moment then parted his jaws just a little. His eyes peered back up at his darling rider’s flushed face. Slowly, very slowly, Toothless’ tip-forked tongue began sliding out between the gap towards the swollen human lust.

Huccup gasped and almost flinched at the attentive touch of Toothless' tongue. His fingers curled against the dragons skin. Hiccup opened his eyes and looked in to large green ones. He wanted something but he wasn't sure he could pin point it let alone bring himself to say it. So he stared almost shyly into Toothless' eyes and just hoped his best friend would chose what was right for them.

 

Toothless didn’t dare break eye contact as he reached his tongue out further and pressed the muscle against his friend’s sensitive body. He pulled back timidly, then touched the member again, pulled back, and finally gauged that Hiccup would allow him to act further. The dragon refused to blink as Hiccup’s body slipped between the slit in his Nightfury’s tongue. 

The taste was even better than the smell alone. Toothless thought about how happy he was that none of the other dragons were anywhere around, and thus couldn’t possibly find him preforming this ungodly act. He wasn’t supremely experienced in matters involving pheromone and hard bodies, but he wasn’t an idiot either. A dragon was a dragon and a human was a human. Between the instinct to know he was doing something taboo and the very serious expression his rider was giving him, Toothless was more than aware that he was treading on dangerous ground. That wouldn’t stop him from doing what he wanted though.

Hiccup had spared his life, fixed the damage he caused, and had since made up for the stupidity of humans a million fold. They were best friends and had been through more than anyone else together. Toothless figured that, as long as Hiccup was good for it, he would gladly break another barrier with the boy.

Toothless’ tongue wiggled up and down, stroking the length of Hiccup’s privates with ease. The fork in his tip allowed him to grip the tender body between his two sections. It felt kind of funny and tickled. He had tried the method a couple times while cleaning himself with pleasant results; he figured that Hiccup would appreciate the trick as well.

Hiccup shuttered and groaned. He closed his eyes as Toothless worked him. "So much better then I'd-" He paused to let a tingle run through him. "-ever imagined." Hiccup fingers slid around searching for a better way to grip Toothless, but the dragon’s scales and lack of hand sized places to grab were making it difficult to get a proper hold. Finally he took hold of the dragon’s ears and knotted his fingers around them. He pulled himself farther up Toothless' muzzle and into his mouth.

 

A quick flinch from the sudden grip on his ears made Hiccup bounce in the Nightfury’s hold. Toothless eyes closed tight then opened back up, more relaxed and with that sassy attitude hinted in their shape. He grinned and began to work his rider’s hard-on into his mouth using the tongue technique he usually saved for fish. Though the human’s girth tasted strangely delicious, he reminded himself to be very careful and not to let the teeth out over it. 

Once the length was completely trapped between his jaws, Toothless gently locked his mouth around the base of the mass and began massaging the member with his tongue and purred. “You taste really good, Hiccup,” he chirped. 

Hiccup moaned his approval of the new technique louder then he meant to, and his blush deepened as he heard himself echo off the cave walls. Despite himself, the purring that was vibrating through his body made it so that he didn’t care. “Toothless” Hiccup moaned again and rocked forward as much as the dragon’s paws would allow him to. 

By gods it was perfect. It was better then flying naked through the night sky. ‘Oh, have to try that.’ Hiccup smiled at the thought and let out a soft giggle as he imagined flying while being with Toothless. He shivered at the thought. That was something he definitely needed to try.

Toothless was watching Hiccup very closing. His rider was making the strangest faces and the most appealing sounds. The taste and smell were incredibly alluring, and Hiccup’s body was getting very warm; that heat was somewhere between soothing and energizing. 

Each half of the dragon’s split tongue moved over his human’s small—or at least it was considerably smaller than Toothless’—prick. As one side moved upward over the head, the other half of the trained muscle would work down the other side of the shaft. It was an art form of play that the green eyed creature had mastered years ago. It was a fantastic way to rotate things in his mouth and served many purposes. Apparently, it also had hidden applications that were just waiting to be discovered and applied. 

Purrs, soft chirps, and little growls escaped the Nightfury’s throat and played off the sound of the Viking’s whines and moans. 

Toothless could feel his own body beginning to excite. It wasn’t something he was used to all that often. Occasionally, he would feel his stomach tighten, his lower belly throb, and then something would happen with his lower body. It would swell up and peek out of its usual hiding place. It usually happened after flying, cleaning, swimming, or wrestling with Hiccup. So when his body began to react to this new form of play, the black-scaled beast just ignored as his bright pink, soft surfaced, stiff form below emerged. He figured he’d take care of it later. However, as Toothless continued to suck on his rider’s lower body, his own body began to become more and more alert. First, it was just the tip of his oddly bright colored member. Then, the small bumps and ridges of its shaft started to appear after the head. Within a few moments, the Nightfury’s hard-on was resting against Hiccup’s leg.

Hiccup shivered as he felt something very warm come to rest against his leg. He had something of an idea of what it could be, but the small part of his mind that was still functioning properly told him he was mistaken. There was simply no way he could have that effect on the dragon. Yes, he was currently getting pleasured by his dragon, but that didn't necessarily mean that Toothless…. Well he didn't really know what that meant at all actually. Either way, he didn't really care right now. That was a mess best saved for later.

Toothless felt Hiccup shiver and cocked his head a little to the side. He wondered if the boy was still cold. In order to warm the boy further, the dragon decided he would try to adjust their positions to suit the purpose. Slowly, carefully, Toothless hugged his rider closer and held him in place as his own legs and tail shifted around under them both to make a kind of pocket. Then, folding in on himself, Toothless bent forward—with Hiccup still in his mouth—and gently laid the human boy down on the ground. 

The spot Toothless placed Hiccup was warm; it had been where the Nightfury had been resting his rump previously. Cautiously, the dragon helped Hiccup lay back against the warm stone and placed the boy’s head on the end girth of his tail. Toothless had eased himself onto his belly and curled around his human to support warmth and pleasure. He managed to ball around his little Viking without ever having to stop suckling. It was a proud feat indeed.

“Are you comfortable?” Toothless purred to his rider. He was always impressed by how lightweight his tiny human way. He seemed to weigh barely anything at all as he leaned back against the dragon’s tail. “Are you warmer?”

He knew trying to speak to Hiccup never really got him very far. Still, it was habit to speak to the boy anyway. 

Hiccup took to the change in position very well. His instinct to trust Toothless overrode his fear at not being in control of his own movements. He gasped as Toothless purred around him once again. His fingers uncurling from the dragon’s ears so that they could roam over the scaly face lovingly. This little nest that had been created was very nice indeed, and really—if it weren’t for the very pleasant distraction currently happening—Hiccup would have loved to fall asleep right then.

Toothless shifted his back end uncomfortably. He had to lift his leg a bit due to his erection causing him some slight discomfort. His back paw lifted off his swollen member and the dragon otherwise ignored for now. He was more interested in the feeling of the soft pets and the unfamiliar taste that was coating his taste buds. 

“This is really fun. You’re behaving sort of strange. I think I like it.” Toothless growled a laugh to himself and smirked a bit. 

His tongue stopped stroking the need and the Nightfury began to lap at his human’s appendage. Thick, wet lick after rough, smooth-tongued lick met Hiccup’s needy form. Toothless was tonguing the boy’s entire lower form now. The dragon had begun an almost cleaning ritual with his Viking lover. His tongue lashed out and caressed the full underside of the boy. The thick fork-tipped muscle was dragged across the surface of Hiccup’s balls and cock several times in relatively quick movements. 

Hiccupped giggled slightly at the new sensation before he shivered and moaned loudly again. His body was beginning to feel tight and hot. He wanted more, but of what? He wasn’t sure he knew exactly. He was also starting to feel a little unnerved. This could change everything, but it was amazing! Fantastic! His body twitched, unconsciously trying to increase contact. He was pretty sure his brain was breaking.  
If this was how sex was meant to feel, then people should have been talking about it more. Much more. If they had told him it would feel this good to be touched by someone else, even a dragon, maybe he wouldn’t have ran from his father. Though, he probably still wouldn’t want to hear about this sort of thing from his father. Still, this was something too good. It all made Hiccup wonder if this was how it felt to be with another person. Then, he wondered if maybe there was something special about being with a dragon.

Toothless’s tongue rolled over Hiccup’s writhing body. One paw was now resting next to the boy. The other was wrapped around Hiccup’s form. Sharp-tipped claws poked gently at the Viking’s soft sides while the dragon’s need throbbed helplessly against the ground. 

The act of lapping at Hiccup’s usually private parts was exciting Toothless to no end. His eyes were still locked on the boy’s face, but his attention was now in his own motions and the effect they were having on Hiccup. It was an experiment: a game to see what buttons trigger what reactions. 

Toothless tried moving slower and watched as Hiccup bit his lower lip. He moved faster and watched the boy’s mouth drop open. Then, he tried to lick just the very top of his human’s lower head and felt the human’s body quake and felt the boy’s delicate finger nails try digging into scales on the top of his head. Finally, curiosity persuaded him. His pink tongue slipped back into his mouth and his jaws clamped shut. He stopped playing with Hiccup’s body all together and just stared at him, eager to see how the boy would respond.

Hiccup whined at the sudden lack of touch; it hurt almost physically. He looked up at Toothless with pleading eyes. When that failed to get him some sort of response right away, he opened his mouth and—Odin help him—he pleaded. "Please." His hand reached up after Toothless' noise. "Please. Just a little more." His voice shook as his fingers brushed over the very tip of Toothless' noise. "Just a little. I wont ask you to after this." He sat up to bring Toothless closer into reach. "Never again." Small tears pooled in his eyes "I promise." The tears began to roll down his face as Toothless just watched him.

A feeling of dread was overtaking hiccup. He had somehow caused this to happen. He had somehow forced his friend into this fowl act. The tears spilled harder and faster. His vision was beginning to blur. Worst of all was that he didn't care right now. All he wanted was for everything to continue, but Toothless seemed to refuse him. He simply would not move. He just watched the young Viking wallow in his misery. He just kept staring.

“Are you crying?” Toothless turned his head to the side. “Really crying?” He had only seen the little Viking cry a few times before. Sometimes when it was too cold or if the boy was punched hard enough, his eyes would water, but this was different. This was strange. Suddenly, the air felt weird. Hiccup was crying, and begging for contact as he sloppily pulled and stroked on Toothless’s face. This wasn’t something the dragon had expected at all. 

The sound of the waterfall had become nothing more than loud background noise. It shielded the noises from within the cave from the outside and it had the force to mask the softer sounds of the giant reptile’s current expression of affection. As Toothless’s eyes soften and his chest heaved with heavier breaths, tiny clicks and chirps vibrated through his sinuses. The noises weren’t like any other sound the black creature had made before. Instinct created them, the way instinct usually dictated the Nightfury’s more passionate experiences. 

Toothless lowered his gaze and eyed the full figure of his beautiful trainer in the dim moonlight that found its way through the falling water at the mouth of the cave. The boy’s seemingly fragile body was laying out before his eyes. His bare chest was moving in violent rolls as he fought a breakdown. His well-forming abdomen was marked in a few small sunspots and the subtle hills and valleys of a man’s chest; muscle had finally started building on the boy earlier that year, and Toothless thought it was a flattering thing to behold. Finally, Toothless took in Hiccup’s strongly erect member. It was small and kind of cute, but there was something about it Toothless hadn’t really considered before.

“This is your…?” His growl trailed off as his eyes met Hiccup’s again. Suddenly, the dragon had a better understanding of what he had done. It wasn’t fully clear, but it was clear enough. His mouth dropped open as he stared at Hiccup wide eyed. 

Hiccup scrubbed at his face, turning away from Toothless. He felt stupid and terrible. What was wrong with him? To think he could do this to Toothless and everything would be fine. Was he some kind of idiot? The twins had to know better then that! God, he was dumber then the twins! Hiccup covered his face with his hands as he took in a shuttering breath.

“Oh.” Toothless looks back down at Hiccup’s length, then back up again. “So you’re crying…” he thinks for a moment then realizes. “It hurts!”

Toothless’s realization comes with a noise of triumph as his head lifts and his body jumps a little. His own dick was beginning to hurt because he’d ignored it so long, and he hadn’t been licking it. Hiccup was in need of more cleaning down there. That was why he was crying! “But why the weird words?” Even if Hiccup couldn’t understand him, the dragon had learned to speak human a lot faster—or at least be able to understand what they were saying—. After a moment of thinking, he thought he figured that part out to. “You’re embarrassed to have me clean you!”

Toothless growled loudly in Hiccups face something the human couldn’t hope to understand. 

“You don’t have to be embarrassed Hiccup. You are my rider, my human, my Viking, my partner. I would clean you the rest of the time if you asked. You don’t need to be ashamed of it. We’re family,” he said plainly. 

Seeing the look of confusion on Hiccup’s face, he decided a physical example was in order. He stretched out his upper body and lifted his arms and legs to show off his belly and his massive hard on. “See? I get them too,” he reassured the boy who didn’t speak his language. 

"I'm sorry!" Hiccup cried out. "I'm so sorry, Toothless!" The boy peaked through his fingers at the dragon's growl and stopped very confused by the sight before him. Toothless was hard. Hard, and putting himself on display. The young Viking blinked several times—his brain having a hard time restarting and processing what was happening.

Without really meaning to, Hiccup reached out and touched the dragon’s hardness. He pulled away sharply, more from the realization that it was in fact real then from anything else. He looked up at Toothless then wiped the last of the tears from his face. The two stared at each other for a long moment before Hiccup looked back at the pink shaft and swallowed. He outstretched his hand once again and carefully ran his finger up the length then around the crown. The dragon trainer was impressed and intrigued as well as aroused. He began to study its shape and texture.

It was soft, which really shouldn’t have surprised him but it did. It was warm too, verging on hot. Though, not too hot. Hiccup liked the felling of it against his fingers. He settled his palms around it and took a few experimental strokes over the entirety of the shaft before cupping on hand over the crown with a swirl of his wrist. He glanced up at Toothless, curious as to what the dragon thought of his actions.

Toothless stared very intently and watched Hiccup as well as he could. At first, it was just very interesting to see that—seemingly all of a sudden—Hiccup had just decided to reach out and grab him. However, after only a quick moment more of Hiccup’s wondering fingers, the sensation could be ignored no longer. 

Dust flew up around Toothless’s upper head as he flopped down completely on his side with a roar. His hips jutted forward slightly and his length pressed into Hiccup’s touch. The sharp thunderous sound that echoed around the room was a verbal sign of the dragon’s affinity for the touch.

Hiccup jumped at the sound then smiled as he realized it was in fact a happy growl, not an angry one. Steading himself Hiccup moved close to Toothless and took hold of him once again. His hands moved gently over the sensitive section of his dragon. He took note and memorized each nub, vain, and dip in the soft flesh.

Before too long, Hiccup licked his lips. A little thought had taken root in his brain. Watching his hands move over the pink flesh of his Nightfury’s sensitives, a small voice in his mind kept asking what it would taste like? Would it be salty? Or would it be gamey? What would it feel like against his tongue? 

Hiccup licked his lips again and swallowed against the nagging questions. Finally he simply gave in and lowered his face to be even with the source of his inquiry. Carefully, tentatively, he opened his mouth and licked broadly across the crown.

Toothless’s growled low in his chest. He slowly rolled his shoulders and moved his head back into a position so that he could see what his rider was up to. Seeing Hiccup’s mouth open, his tony tongue still lolling out in the open, the dragon cooed and rose what could be described as his eyebrow at the boy. “Are you going to try cleaning me now?”

Hiccup pulled away, glancing away from Toothless face. Maybe this wasn't a good idea after all.

He rolled the taste around on his tongue and tried to decipher it. It wasn't so much fishy as it had a very water-based animal flavor to it. It certainly wasn't bad, though he wasn't quite sure how to describe it. If he had to say anything—based on just the one taste—he would say it tasted like, well, like Toothless. And that didn't explain anything.

Toothless reached out and pushed Hiccup closer to his exposed bits. He wanted to encourage the boy to continue in whatever it was the boy thought he was doing. Though, at this point, it was rather clear that Hiccup had no chance of being able to help clean the dragon. Toothless still wanted his rider to keep touching him. That was okay, wasn’t it? 

Hiccup was shoved towards the mass again by the eager dragon who was staring very interestedly at him now. His eyes were large and cat-like again. He was making that cute expression that suggested he was trying to figure something out or learn. It was Hiccup’s job to teach him things about humans, just like it was Toothless’s job to teach Hiccup about dragons.

Hiccup glanced up at Toothless wide eyes. Maybe the licking had been a good idea after all? So, still watching the dragon's face he opened his mouth again and licked up the side of the shaft sliding his hand up behind his tongue.

Toothless licked his lips as he watched, intrigued. It felt good. No. It felt great. It was unreasonable, but it was still true. This tiny little Viking with its itty-bitty tongue was managing to stimulate something very primal and enjoyable. Toothless was a bit baffled. How could Hiccup be so amazing at everything? It really didn’t make sense. Based on size, smell, and texture alone, Hiccup’s soft tongue shouldn’t be able to preform usefully for anything other than speaking in Norse jibber-jabber and devouring things. Yet, sure enough as it takes two tail fins to fly, Hiccup was sending shivers up and down Toothless’s spine. How was it even possible?

Toothless waited and watched. He nodded slowly, “Again.”

Hiccup smiled despite himself at the nod Toothless gave him. So, when he came to the very tip with his tongue he retuned to the base and repeated the proses right next to where he had just licked. He did this again and again until he had to flip around so that his back pressed against Toothless’ body in order to reach the other side of the erection. Then he continued, bringing his other hand up to wrap around the shaft.

Toothless watched in awe. The Viking boy was practically straddling his cock and he was stroking the form with his hands, his mouth, and even his torso at times. It was somewhat amusing, and somewhat something else that he wasn’t sure how to explain. Simply, the feeling made his dick swell to a fuller size and it made his mind feel dizzy and floaty. A soft growl escaped the dragon, and then a little roar followed, “Gods, that’s good!” 

The Nightfury stretched his hind legs out and apart to allow the boy more freedom to move and work his magic. His right wing shifted underneath him and his left stretched out into the air before folding back in place. Toothless couldn’t help but fidget. He was starting to get restless. 

He eyed Hiccup and felt himself starting to salivate as the boy continued to suckle, nip, and slurp at the massive dragon cock. “Do you like the taste?” he growled at his trainer. Hiccup didn’t respond; he just kept on at it. Toothless mused to himself about how enticing Hiccup looked, his skin now gleaming in the dim moonlight with the help of a film of moisture that was beginning to coat his skins from his oral efforts and rubbing up on the moistened length. 

The boy smelt as good as he felt. A heavy musk was building around them both and the stench was beginning to make Toothless feel the need to become more active. Suddenly, as his mass grew to full size, Toothless felt the dull growing pain of needing to rub off on something. He had only felt the ache a few times before. Usually he could just ignore the arousal until his prick went back in its pouch. However, there had been a few times when flying too long with Hiccup bouncing around on his back or the boy’s strange smells would leave the poor Nightfury with a boner that was too hard to just get rid of. When that happened, he usually rubbed off on some defenseless river stone or he rolled in the fields of soft, sweet smelling grass until it was dealt with. 

Neither was an option. 

Hiccup and Toothless had been pulled from their home world through the strange cloud so there were no sweet grass fields or large smooth boulders to harass. As the dragon watched his rider work his way around his excited, sore, and swollen form he got an idea. It was a kind of strange and almost wicked idea, and he wasn’t sure if it would work. He was determined to find out though.

A devilish look darkened the dragon’s expression. A low, mischievous growl vibrated deep in his belly. His tail slid out of sight as it prepared for the next move. Without being noticed, his upper torso shifted so that it was parallel to the ground, ready to lift up. It wasn’t until the Nightfury was ready to attack that Hiccup finally realized his dragon was changing position. 

“Wha-,” Hiccup’s face was covered in the drool he’d lubed Toothless’s hard on with. He panted as he tried to catch his breath from all the excitement. Toothless was getting up. ‘Is he trying to leave me? Did I do something wrong?’ he thought. “What are you doing, buddy?”

In a flash, Toothless had managed to knock Hiccup to the ground and had gotten over him. At first, the reptile’s face hovered over his trainer’s. Hiccup’s hands were up by his head defensively open to show he wasn’t a threat. As the human stuttered about his confusion, Toothless made his move. 

The black scaled of the dragon’s chin, neck, then chest rushed over Hiccup’s line of sight. Toothless was standing over him, and now the Nightfury was walking over him. The movements were questioned for a short moment before some of the dragon’s intentions became clear. 

Toothless stopped when his solid cock had managed to run along the length of the Viking’s body. The smaller male’s face was now met with the dripping tip of his pet’s bulbous member and belly. Then, the dragon did a little dance to adjust his four legs to better steady himself before he arched his back and began pressing his entire length against his naked companion. 

Toothless, the enormous black dragon was hunched over and rubbing his massive cock off on the nude form of his much smaller human friend.


	5. Lesson One: Teaching Through Example

**Summary for the Chapter:**

> Jack returns to the cave to find Toothless and Hiccup doing something completely queer. Being unfamiliar with any sort of sexual behaviors, Frost is fascinated as he bares witness to an otherwise beautiful union of Dragon and Rider. He's caught peeping though and his ignorance isn't excuse enough for his rude behavior.

**Notes for the Chapter:**

> Finishing up the Toothless/Hiccup scene!  
> Hope you all like it. This starts getting Jack involved and will lead to future fun. Hope you all like it. :)

Jack had ventured into the human town to find something that could be used to bring his two new physical friends comfort. After a little effort, he finally managed to find three large blankets that he hoped would do the trick. 

As the winter spirit glided back towards the cave on icy winds, he mused to himself about how interesting the day had really been. He’d met a dragon and a rider who had known nothing about him, and yet could see and interact with him as if they were guardians themselves. Then, there were the magical lights they said they traveled through. A different world, what an idea!

“Oh Bunny would get his tail in a twist if he knew about this,” he laughed to himself. He wondered if his Guardian friends knew anything about other worlds. “Santa’s got those cool space orbs. Maybe he has ones that can take you to other worlds too.” 

Jack considered the idea as his feet led him from branch to branch in the wood’s treetops. He glanced up at the moon and thought to himself, “You would know, wouldn’t you?”  
As Jack looked back to the trail towards the cave, he saw something bright that caught his attention. He knew he shouldn’t veer from his path, but the sparkling object was too interesting to pass up. He decided he’d just take a quick look, and then get back to his new companions. It would only take a second.

Jack rushed toward the strange glistening light. His eyes were bright with curiosity. Just when he thought he was near it, the object seemed to shift away. It relocated further away, further from the cave. Jack’s head tilted to the side. He wondered if some sort of creature was causing the light. He hadn’t known any creatures in the woods to emit that sort of glow before, but he had never known a dragon to exist in his woods either. 

Jack continued to follow the light around for quite a while before he finally remembered his task. He looked down at the blankets in his hands. The light didn’t seem to be disappearing, just moving about. He could probably find it again if he was quick about dropping off the blankets to his living companions. They needed warmth more than he needed to sate his curiosity; this was a rule of order Jack had learned when he had lost Baby Tooth back during the nightmarish attack by the Boogieman. Friends always came first. Curiosity was second.

When Frost turned to head back towards the cave and started for it, the light appeared in front of him. It seemed to be legitimately trying to get his attention now. After he had neared the entrance, he had been met face to face with the source of light. In fact, it wasn’t so much a source as it was light itself.

“A moon beam?” Jack’s right eyebrow lifted far higher than his left. This wasn’t something he’d expected at all. In front of him, a moonbeam—a very concentrated and life like moonbeam that seemed to be able to redirect itself anywhere—was floating in front of his face. As his eye focused on the thing, it moved away from him and his attention followed it. Jack smiled, playfully amused by the bouncing light’s movements. “How are you doing that?” 

Jack giggled and started following the beam back into the woods. Then, something loud came roaring from behind him. 

The dragon? Was that Toothless?

Jack flew to the cave entrance quickly. There didn’t seem to be any kind of struggle by the look of the outside of the cave. He ventured inside. Some of the water froze as he passed the waterfall. When he got inside, he couldn’t see Hiccup and it worried him. However, he did see Toothless. He was about to move forward when he head Hiccup’s voice.

Hiccup arched up against Toothless his hands sliding over the scaly under belly as he moaned for more in a needy drawn-out take of the dragon’s name.

Toothless gave a deep growled purr and continued thrusting over his rider’s naked body.

Jack nearly landed when he thought better of making any noise that might draw attention to him. He wanted to know what the two were up to. He felt a familiar tingle of being naughty by being there unnoticed and he didn’t want them stop whatever they were doing before he could get a better look. 

Carefully, Frost lowered the blankets onto the ground then used the winds to help him creep over towards the two shifting foreigners. As he moved closer, he finally got a glimpse of the human. Hiccup was hidden under the mass of his Nightfury friend. 

“Are the wrestling?” Jack thought to himself. He moved closer and watched intently as the mass of black scales continued to rock against the ground and apparently the little Vikings form. “Why is he moving like that?” 

Hiccup's eyes were shut and little pants were escaping his parted lips. Any feeling of coldness had long since left him, but then a soft cold breeze managed to work its way between the two friends and across his side. A shiver ran through him, but if it managed to do anything it managed to push him to try and coax Toothless down onto him more.

Toothless’s teeth had managed to slide out into view. He was snarling in something Jack couldn’t quite register; rough lust. 

As Jack floated around to catch a side view, he nearly got smacked in the face with one of the dragon’s wings as it stretched and replaced itself at a half span. The beast was tense and there was a strange smell in the room. Jack placed the end of his staff on the ground and took his place on top of it. From his perch he watched curiously with a cocky smirk on his face and fascinated eyes. He’d never seen anything so strange in his life.

Toothless let out another loud growl and lower his hips further as he continued to thrust. His length was grinding over Hiccup’s bare flesh and precum had started to leak out from the excitement. The mess was being smeared over the whole of the Viking’s form. 

Jack’s head lurched down and turned to the side as he tried to figure out what was happening. Toothless back legs adjusted and Jack saw a better glimpse of Hiccup’s wet, naked body and something big and pink. The heat radiating off the two other-worlders was intense, even for the son of winter. He felt himself becoming more curious and the feeling of being naughty was getting stronger too.  
Hiccup licked the salty liquid from his lips before easing his eyes open once again. He wanted…- He swallowed hard as he saw the slick liquid beading and sliding down the warm pink shaft as it rubbed against him. -…He wanted Toothless in his mouth. Yes. Yes, that was exactly what he wanted, but he also wanted what was happening to continue. He wasn't quite sure how to have both. Maybe he could… oh yes! That would do nicely. 

With a little bit of a fighting wiggle he slid a bit further under Toothless and craned his neck so that with each of Toothless' thrusts the tip of his shaft slid between his lips. It was an odd sensation, but it was also exactly what he had been missing. He lapped at the tip as it moved over his body and deeper into his mouth.

Jack’s eyes widened and his mouth dropped open. As he stared intently, a frantic moonbeam entered the cave through the waterfall and tried to blind the Guardian. Jack simply lifted a head to shield his face from the light source. The moonbeam glinted frantically trying to draw Jack’s attention away. It didn’t work.

Frost decided he needed a closer look. The white-haired boy jumped off of his stick, landed soundlessly on the ground, and quietly stepped closer to the two playing body masses. As he moved to Toothless’s side, he bent down with his knees and examined the goings-on more closely. 

Toothless was thrusting a growling rapidly now. A small trail of saliva dribbled from between his parted jaws. There was an underlying sound of whining echoing from his throat. “Hiccup,” he moaned in a voice neither the winter spirit nor Viking could understand. 

Scales rubbed against the soft top of the dragon rider’s head, as the Nightfury buried is snout into the boy’s hair. Then, the huge reptile lifted his head up and back. His eyes were closed and his hips continued to beat forward with determination. 

The sight was messy and the smell was somewhere between enticing and fowl. Jack’s head cocked to one side while he bent lower and moved closer. He could now see the large pink organ and the boy it was assaulting more clearly. The image was engraving itself into his memory and it made him feel very strange indeed.

Hiccup groaned around Toothless’s dick as the dragon's moan rumbled through him. His eyes fell shut as Toothless nuzzled the top of his head while his own mouth locked around the slightly pulsating head.  
The chill was becoming more persistent, but Hiccup focused on the task at lip.

Jack was now unreasonably close. His natural cool skin and breath were leaving small misty clouds around the two hot bodies where they nearly met his own form. His scent was that of fresh morning snow; it wasn’t something that even Toothless thought anything of. The night had been a cold one when they entered the cave and the smell didn’t set of any alarms. Living amongst Vikings, Toothless was confident he would know if a human was coming to sneak up on him.

Toothless’s base began to swell thicker. His glands turned a bright red as his body began to reach its breaking point. Eight large front talons sliced at the stone floor of the cave. The beast’s chest heaved as he panted and his teeth glistened with drool as he snarled. 

Jack felt something turn in his belly as he watched. Timidly, he reached a hand out. He wanted to touch the strange throbbing organ. He’d never seen anything like it before and he had more questions than simple curiosities. The first were, “What is it and what does it feel like?” As he inwardly wondered about these things, he moved cautiously towards where the length met the rider. Then, Frost asked his first question out loud; the one that seemed the most appropriate to start with.

“What are you doing?” 

Hiccup’s eyes snapped open as a voice rang out close to him. His mouth released Toothless and a startled scream erupted from him. Jack was back and very very close to him as he writhed under his dragon. This was far from an ideal moment. Truth be told, the young Viking wanted to vanish under his dragon completely; though, he didn't see how that was an option. Hiccup's already flush stained cheeks darkened with embarrassment as his hand flew up to hide his shamed face. Since he couldn't vanish all together, he figured he could at least keep himself from looking at the other boy. 

"Get out!" he screamed, trying to hide himself as much as possible.

Jack’s eyes widened in confusion and defensiveness. His hand snapped back away from the two and it was probably good it did, because at the moment that Hiccup barked his order Toothless’s eyes had opened and a violent anger filled him. 

The dragon turned and snapped at Jack with a loud clap as his jaws locked shut in front of Frost’s face. 

“Whow!” Jack jumped back onto the cave wall as Toothless growled and hissed threateningly in his direction.

Hiccup wrapped his arms around as much of Toothless as he could. As much as he was unhappy with Jack's presence he didn't want the other boy hurt. Moreover, Jack was the only person they knew the world they were in now and was their only chance at getting home. "Toothless." He tried to sound authoritive, but ended up sounding frightened and small.

Toothless wasn’t going to have some winter nymph intruding on his relations. A charge blast built up in his chest. Jack saw the light in the dragon’s mouth before he smelt the stench that came with the heated fumes. As the blast shot out between the Nightfury’s lips, Jack darted out of the way with natural grace. Once the strange sound rumbled in the dragon’s chest again, Jack took the hint and darted out of the cave in a swift dash. 

Hiccup started as Toothless sent out the first blast. It was a strange sensation: the plasma blast. He had certainly felt them from atop the dragon, but to be under him when he did it was an altogether new sensation, and not a bad one at all. He groaned as Toothless charged a second blast.

Toothless gave a loud growl and a smart nod. Turning his attention back to his rider his eyes became less intense. His head lowered and pressed to Hiccup’s chest. He gave a whine to apologize for the interruption. 

Hiccup nuzzled his face against Toothless's with a soft sigh. The interruption had startled and somewhat upset him, but it by no means had stopped or ended the building orgasm. The show of power that Toothless had just put on had only served to return and strengthen it.

Another moment without complication would yield a tremendous climax for the eager green-eyed reptile. His body was throbbing and he was eager to finish. However, despite his fervor he had finally come to a realization of what it was he thought he was doing. He looked down at his trainer and wondered for a moment if the boy was now something else to him: something closer to a real partner. Toothless certainly felt as though he and Hiccup were closer.

The dragon sniffed his rider’s face and then licked the mess he’d made off the boy’s cheeks. His teeth were put away and his tail was fidgeting behind him. Toothless’s eyes quickly looked the boy over and begged to ask the question, “What now? Can I keep going? What are we doing?”

Hiccup moaned contently as Toothless licked his cheeks. He had been licked many times before, but this felt much more intimate. He spread his legs farther apart and pressed himself against his friend. He needed the last few pushes, then the pressure that had built up inside him would leave him and he wouldn't feel quite so thinly spread. He needed Toothless to, as his father put it, “claim him”.

Toothless looked down towards his hard-on and his master’s twitching prick. He looked at his own needy dripper and decided the natural thing to do would be to press his body to Hiccup’s. The endeavor ended more favorably than he hoped. 

The dragon’s back legs adjusted repeatedly as his form backed up some so that his penile glands were pressed to the delicate spots between Hiccup’s thighs. His precum quickly coated Hiccup’s member in a thick, sticky film. When his hips started to thrust again, Toothless moaned loudly and shook his head. His tip was now ramming into the base of the Viking’s pelvis. It was pressing hard against his ass and balls while occasionally slipping up over the boy’s groin up to his navel and back down for a few more solid thrusts into the base again. 

Hiccup’s head lolled back and his fingers fisted around a claw on each side of him. His hips rocked to meet Toothless's thrust. "Toothless," Hiccup gasped. His fingers tightened as his back began to arch.

Toothless panted and sped up. As his pace quickened, the surge came on hard again. His lower stomach tightened and ached as he arched downward growling his lover’s name against his ear. The tip of his lower head lubed the smaller male’s entire lower body. Each time the lizard pulled back, thick stings left behind a connection between the tip to Hiccup’s flushed ass.

Hiccup shivered, bit down on his lip, then growled Toothless's name as the tight rope that was strung within him snapped and he came. His nails dug into the dirty stone under and around Toothless's claws.  
His back arched off the stone pressing his fevered skin against the warm underbelly scales.

Toothless sniffed the air. His eyes slit and his teeth crept out once again. He let out a roar and pressed his body hard against his smaller companion’s. His body broke just after Hiccup’s. The tips of his wings scraped the ceiling of the cave as the two limbs extended from the tense sensation overwhelming Toothless’s mind and body. The fluid that splashed from his body fell heavy on Hiccup’s. His hips trembled and his roar dulled to a growl, then to a moan, and finally to an exhausted pleased whimper. 

As Toothless’s body rolled over onto its side so that the dragon was now lying next to Hiccup’s, Jack swallowed a lump in his throat. 

He’d managed to sneak back in and witnessed the finale for himself. Now that both of his new friends were lying on the cave floor panting and dripping in some kind of bodily fluid, Frost felt his endless childish curiosity overtake him once again. He wanted little more than to venture over and harass Hiccup with questions, but with that brute of a guard dog over there he decided to keep his distance.

Toothless stretched out his legs to cool off his underbelly and allow his growing softer length to have the freedom to relax and retract. His belly bounced as he panted. His tongue lolled lightly from the side of his mouth for a moment. After a moment, he swallowed and closed his mouth. His nostrils flared with his still restless breaths, but he was regaining his thoughts. He turned his face to the side so that he could look over his handsome partner.

“That was fun,” he purred.

Hiccup lay panting, staring at the ceiling. He was splattered in—what almost amounted to—a blanket of dragon spunk, and all that he could think of it was that he wanted to do it again. Perhaps not right now, later, most definitely later. Now a long sleep was in order. He turned to Toothless when he purred and smiled. Their green eyes met and the moment of complete understanding pasted between them. Hiccup's smile fell as he noticed Jack's refection in Toothless's eyes. The winter spirit was watching them from the far corner. Hiccup's head whipped around toward their observer.

Having being spotted, Jack’s face creased with a broad, playful smile. He knew he had done something inappropriate by watching the ends of the foreigner’s engagement, but he had been intrigued and being mischievous was kind of his natural setting. Instead of apologizing, he giggled. Instead of making a bigger deal out of the matter, he raised a long pale finger and pointed to the pile of blankets resting near the two sated males. 

Hiccup begrudgingly turned and looked at the small pile of blankets. Good manners dictate that he thank Jack for the blanket. Though, good manners also dictate that he not call Jack a pervert and he really, really wanted too. He wanted to get up and scream it at him, not that screaming would do much good, but Hiccup had the sneaking suspicion that he would feel a lot better for it. What’s more, he’s a Viking! So who the hell cares about good manners? 

Finally snapping his attention back on Jack, Hiccup glared and growled, “Thanks, pervert,” before he rolled over and, using one of the blankets like a towel, wiped himself as clean as he could. Then, wrapped himself in the other as he sat down next to Toothless and continued his glare at the winter boy. “Well? Do you have anything to say for yourself, Pervert?”

Jack laughed, feeling very naughty. “Pervert?” His head nearly rolled his head til it was upside down. “I’ve never been called that before.” 

With Hiccup eyeing him the way he was, Frost felt incredibly playful. He was in trouble, but he didn’t feel like it was particularly threatening. So, he was enjoying himself.

Toothless looked over at the winter spirit and growled. “Do you want me to roast him, Hiccup?”

"Maybe…" Hiccup growled, but let the rest of his budding threat fall flat.

Toothless lifted his tail and wrapped it around his Viking mate and himself and gave Jack a very ignored feeling. The dragon purred a low, “Good night,” to his rider before taking his last deep breath before he began to rest.

Jack floated up overhead and eyed the two strangers with some disappointment. The Sandman visited the children of the world and sleep seemed to find everyone else. Everyone at least, except him. Jack didn’t sleep, and it was more than disappointing to have a new friend that needed rest. He wanted to play more and ask questions. 

Hiccup curled against Toothless and closed his eyes ignoring the floating boy. Sleep was pulling against his eyes anyway. With this, he wouldn't have to deal with anything until morning. So, with a soft sigh and a quite "Good night, Toothless" the young Viking drifted off to sleep.

Jack watched the two for a long moment, then sighed and floated out of the cave in an eager motion. “Now what am I suppose to do?”

**Notes for the Chapter:**

> I'm very sorry to announce that, due to personal relation issues, this fiction is currently on hiatus.   
> This problem may be resolved in the future, but for now, we have no way of knowing when or if this project will continue.


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